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The holiday season on Anna Maria Island is nothing short of magical. With its tropical charm, stunning sunsets, and a strong sense of community, Anna Maria Island transforms into a festive paradise where holiday cheer meets island vibes. Whether you're visiting for Christmas or ringing in the New Year, the island offers a variety of holiday events, parades, and celebrations, as well as Christmas church services that add a spiritual dimension to the season.

At Once Upon A Beach, we know that Halloween is a cherished holiday for families, and there’s no better place to enjoy the spooky fun than right here on the island. Whether you're staying in one of our luxury vacation rentals or exploring the island with your little goblins and ghosts, here’s everything you need to know about trick-or-treating on Anna Maria Island and how to make the most of your Halloween adventure.

Football season is always an exciting time, whether you're a passionate NFL fan, following college football, or simply enjoying the camaraderie and excitement of game day. If you're visiting or staying on Anna Maria Island and don’t want to miss out on the big game, you’re in luck. The island and its nearby areas offer a variety of lively sports bars where you can cheer for your favorite team, enjoy great food, and catch all the action on the big screen.

While Anna Maria Island offers plenty of upscale dining options and beachfront cafes, sometimes all you want is a cold drink, good company, and a no-frills environment. That’s where Anna Maria Island’s dive bars come in. These local watering holes are perfect for anyone looking for a casual, fun night out with a little grit and plenty of character.

There’s something undeniably romantic about exchanging vows on a pristine beach with the gentle sound of waves in the background and the sun setting over the Gulf of Mexico. Anna Maria Island, with its stunning beaches, laid-back charm, and intimate atmosphere, is the perfect destination for a luxurious beachside wedding. Whether you’re envisioning a grand celebration or a more intimate gathering, hosting your wedding on Anna Maria Island offers a picturesque backdrop for your special day.

Anna Maria Island is more than just a picturesque destination with white sandy beaches and turquoise waters. Beyond the stunning sunsets and tranquil atmosphere, the island offers a treasure trove of shopping experiences that range from chic boutiques to charming local shops. Whether you're looking for one-of-a-kind souvenirs, stylish beachwear, or locally-made artisan goods, shopping on Anna Maria Island is an essential part of your vacation experience.

There’s something magical about relaxing on Anna Maria Island, where the stunning beaches and beautiful sunsets pair perfectly with live music. Whether you’re looking for laid-back acoustic sets with ocean views or a lively night out dancing to local bands, Anna Maria Island and its surrounding areas offer a variety of live music venues for every mood.

Known for its thrilling theme parks, beautiful beaches, and year-round sunshine, Florida offers a perfect blend of excitement and relaxation. But why settle for just one type of vacation when you can have both? By staying on the stunning shores of Anna Maria Island and combining your trip with a visit to world-class attractions like Busch Gardens, Universal Studios, or Disney World, you can experience the best of both worlds—a beachside retreat and thrilling theme park adventures.

Anna Maria Island is known for its beaches, and relaxed island lifestyle. Especially in paradise, you deserve to look and feel your best. Whether you’re here for a romantic getaway, or simply treating yourself to a little pampering, Anna Maria Island is home to several excellent salons that specialize in hair and nail services. From cutting-edge cuts and color to luxurious manicures and pedicures, these salons offer the perfect mix of professional expertise and island charm.

At Once Upon A Beach, we believe that fine dining is an integral part of any luxury vacation, and we want to help you discover the best restaurants during your stay. Here’s our curated list of the top 10 fine dining restaurants within 15 miles of Anna Maria Island that will elevate your dining experience to the next level.